Methanol → HCID 68183455, compound

HRID 513739Notes

Reaction equation

HRID 513739 reaction equation
O=S(Cl)Cl.[N+:5]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[C:13]2[C:18]([OH:20])=[O:19])([O-:7])=[O:6].[CH3:21]O>>[CH3:21][O:19][C:18]([C:13]1[C:12]2[C:17](=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=[CH:10][CH:11]=2)[N:16]=[CH:15][CH:14]=1)=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 14226197HCID 14226197, compound

Product 1

HCID 68183455HCID 68183455, compoundYield 22%

Conditions

Temperature
70 °C

Procedure

SOCl2 (10 ml, 137 mmol) was added slowly to 8-nitro-quinoline-4-carboxylic acid 473 (3.0 g, 13.8 mmol) in MeOH (40 ml) and the mixture was heated at 70° C. for 7 h. After cooling, the solvent was removed in vacuo and the residue was diluted with EtOAc. The organic phase was washed with sat. NaHCO3 solution and brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (95:5) as the eluent to give the title compound (0.70 g, 22%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. additionthe residue was diluted with EtOAc
  4. washThe organic phase was washed with sat. NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (95:5) as the eluent

Sources & evidence

ORD record
ord-3475938a5cc1463381028980e4e07e1b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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